A fierce leader and a cache of weapons helped make the Galloway Boys one of the most feared street gangs in Toronto, but today they pose a new threat with younger members vying to fill a leadership vacuum.

Toronto police have linked the street gang to three homicides and six shootings that occurred in the city over an 11-month period, stretching from Sept. 4, 2011 to Aug. 10, 2012.

Those incidents included the deadly shootout on Danzig Street this summer, as well as the killing of a man that police allege was shot after gang members mistook him for another target.

At a news conference on Tuesday, Det. Sgt. Brett Nicol told reporters that police have learned that the Galloway Boys are currently in conflict with a group from the Orton Park area.

But Nicol said the violence "is being fuelled by the Galloway Boys’ propensity for violence, their ability to obtain guns and their willingness to seek revenge."

Nicol said the members linked to the shootings in Toronto are believed to be jostling for control within the gang.

Prior to Tuesday’s news conference, police had made clear that a new generation of leaders was coming into play within the Galloway Boys organization.

The Riley years

Anthony Hutchinson, a court-certified gang expert, said the Galloway Boys name appears to come from police, as the group has had other names on the street during its long history.

Years ago, the street gang was led by Tyshan Riley, who came to power after a close friend, Norris Allen, was shot dead while sitting in a parked car in October 2002.

Hutchinson said the Riley-era Galloway Boys were highly organized and involved in a number of criminal enterprises.

"The Galloway Boys unlike most other gangs across the City of Toronto were involved in everything: crack, prostitution, arms trades, gun trades, munition trades, whatever they needed to do to make money," Hutchinson said in an interview with CBC Radio’s Metro Morning.

In late 2003, the gang came into possession of a cache of guns that they obtained through theft.

"It was because of their arsenal that they were probably the most powerful gang … in Toronto in recent years," Hutchinson said.


Toronto police Det. Sgt. Brett Nicol said the Galloway Boys are involved in a conflict with a group from Orton Park. (CBC)

But despite the firepower at their disposal, the police would eventually manage to dismantle much of the gang and put its leadership behind bars.

Toronto Star court reporter Betsy Powell wrote a book about the Galloway Boys, including their lengthy feud with the Malvern Crew, a rival street gang.

She told Metro Morning earlier this year that the Galloway Boys became the focus of a police investigation after the killings that Riley was involved with.

Riley and two other Galloway Boys are each serving a life sentence for a March 2004 attack on two innocent men who were mistakenly believed to be members of a rival gang.

Last year, Riley was also handed an 18-year sentence after being convicted on two counts of attempted murder, which related to an April 2009 incident that left two other men wounded.

Opportunity knocks

When Riley was put behind bars, a new opportunity opened up for potential successors.

"Once he’s out of the picture, what happens is you have a lot of up-and-comers, or kind of hangers-on to the people affiliated with [the Galloway Boys]," said Hutchinson. 

Without a single leader in control, Hutchinson said it is likely that there will be competing groups vying for control of the organization.

"That's going to be a lot more dangerous, not just for that community, but for Toronto as a whole," he said.

Nicol said that some of the Galloway Boys that were locked up in the past have slowly been let back out into society.

And some of them have helped bring along the successors that have stepped into their shoes.

"They were considered mentors to the young members that we’re now seeking today," he said.

It remains to be seen whether Riley still holds any sway with the gang.

Riley’s voice has been featured on at least one rap song posted online, which includes audio of the former Galloway Boys leader talking on a telephone.

Powell told CBC News on Tuesday that she has heard reports that some people look upon Riley as a kind of hero.